HCID 178522995, compound → 5-benzyloxy-N-(4-fluoro-benzyl)-6-formyl-4-hydroxy-nicotinic acid amide

HRID 1622917Notes

Reaction equation

HRID 1622917 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:27][OH:28])=[N:11][CH:12]=[C:13]([C:25]=1[OH:26])[C:14]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[C:10]([CH:27]=[O:28])=[N:11][CH:12]=[C:13]([C:25]=1[OH:26])[C:14]([NH:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178522995HCID 178522995, compound

Product 1

HCID 1785199845-benzyloxy-N-(4-fluoro-benzyl)-6-formyl-4-hydroxy-nicotinic acid amideYield 84.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

After manganese dioxide (49 g) was added to a suspension of the compound 10 (9.8 g, 25.6 mmol) in chloroform (490 ml), the mixture was stirred at room temperature for 1 hour. After the reaction solution was stirred at 60° C. for 20 minutes, Celite filtration was performed, and this was washed with chloroform heated at 50° C. The filtrate was distilled off under reduced pressure to obtain 5-benzyloxy-N-(4-fluoro-benzyl)-6-formyl-4-hydroxy-nicotinic acid amide 12 (8.2 g, 84%) as a pale yellow crystal.

Workup

  1. stirringAfter the reaction solution was stirred at 60° C. for 20 minutes
  2. filtrationCelite filtration
  3. washthis was washed with chloroform
  4. temperatureheated at 50° C
  5. distillationThe filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8d140a9cc305466fa517b7038d5cd3db
Source dataset
uspto-grants-2014_07
Patent number
US08778943B2

Reaction notes

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